Microbiocidal oxadiazole derivatives

Abstract

Compounds of the Formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.

What is claimed is: 
     
         1 . A compound of Formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         n is 0, 1, or 2; 
         A 1  represents N or CR 1 , wherein R 1  represents hydrogen, halogen, or methyl; 
         A 2  represents N or CR 2 , wherein R 2  represents hydrogen, halogen, or methyl; 
         A 3  represents N or CR 3 , wherein R 3  represents hydrogen or fluoro; 
         A 4  represents N or CR 4 , wherein R 4  represents hydrogen or fluoro; and 
         wherein at least 2 of A 1 , A 2 , A 3  and A 4  are C—H; 
         R 5  and R 6  independently represent hydrogen, methyl, cyano, difluoromethyl, or trifluoromethyl; 
         R 7  represents hydrogen, hydroxy, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, hydroxyC 2-4 alkyl, C 1-2 alkoxyC 2-4 alkyl, C 1-2 haloalkoxy, C 1-2 haloalkoxyC 2-4 alkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 3-4 alkenyloxy, C 3-4 alkynyloxy, C 1-4 alkylcarbonyloxy, C 3-6 cycloalkyl, or C 3-6 cycloalkylC 1-2 alkyl; 
         Z represents R 8 , wherein 
         R 8  is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, cyanoC 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxyC 2-4 alkyl, C 1-2 haloalkoxyC 2-4 alkyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylcarbonyloxyC 2-4 alkyl, N—C 1-4 alkylaminocarbonylC 1-4 alkyl, N,N-diC 1-4 alkylaminocarbonylC 1-4 alkyl, N—C 1-4 alkylaminoC 2-5 alkyl, N,N-diC 1-4 alkylaminoC 2-5 alkyl, C 1-3 alkylcarbonylaminoC 2-5 alkyl, or C 1-4 alkoxycarbonylaminoC 2-5 alkyl; or 
         R 8  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl or heteroarylC 1-2 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl or heterocyclylC 1-2 alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S; 
         wherein when R 8  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl, heteroarylC 1-2 alkyl, heterocyclyl, or heterocyclylC 1-2 alkyl, the C 3-6 cycloalkyl, phenyl, heteroaryl, or heterocyclyl motif is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 ; 
         R 9  represents cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; and wherein when R 8  is substituted C 3-6 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C═O) or sulfonyl (S(O) 2 ) group; or 
         Z represents —N(R 10 )R 11 , wherein 
         R 10  represents hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, cyanoC 1-4 alkyl, hydroxyC 2-4 alkyl, C 1-2 alkoxyC 2-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, aminoC 2-4 alkyl, N—C 1-4 alkylaminoC 2-4 alkyl, N,N-diC 1-4 alkylaminoC 2-4 alkyl, formyl, C 1-4 alkylcarbonyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylcarbonyloxyC 1-4 alkyl, N—C 1-4 alkylaminocarbonylC 1-4 alkyl, N,N-diC 1-4 alkylaminocarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylaminoC 2-4 alkyl, C 1-4 alkylcarbonylaminoC 2-4 alkyl, or C 1-4 haloalkylcarbonylaminoC 2-4 alkyl; or 
         R 10  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl or heteroarylC 1-2 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl or heterocyclylC 1-2 alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S; 
         wherein when R 10  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenylC 1-2 alkyl, phenyl, heteroaryl, heteroarylC 1-2 alkyl, heterocyclyl, or heterocyclylC 1-2 alkyl, the C 3-6 cycloalkyl, phenyl, heteroaryl, or heterocyclyl motif is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 12 ; 
         R 12  represents cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; and wherein when R 10  is substituted C 3-6 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C═O) or sulfonyl (S(O) 2 ) group; 
         R 11  represents hydrogen, hydroxyl, C 1-4 alkyl, C 1-2 haloalkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 3-4 cycloalkyl, C 3-4 cycloalkylC 1-2 alkyl, C 1-4 alkoxy, C 3-4 alkenyloxy, or C 3-4 alkynyloxy; or a salt or an N-oxide thereof. 
       
     
     
         2 . A compound according to  claim 1 , wherein A 1  and A 2  each independently represent N, C—H or C—F, and A 3  and A 4  each independently represent C—H or C—F, wherein at least 2 of A 1 , A 2 , A 3  and A 4  are C—H. 
     
     
         3 . A compound according to  claim 1 , wherein R 7  is hydrogen, methyl, ethyl, n-propyl, isopropyl, methoxy, cyclopropyl or cyclopropylmethyl. 
     
     
         4 . A compound according to  claim 1 , wherein R 5  and R 6  independently represent hydrogen or methyl. 
     
     
         5 . A compound according to  claim 1 , wherein Z represents R 8 , wherein R 8  is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, cyanoC 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxyC 2-4 alkyl, C 1-2 haloalkoxyC 2-4 alkyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, or C 1-4 alkylcarbonyloxyC 2-4 alkyl; or
 R 8  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl or heteroarylC 1-2 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, or 3 heteroatoms individually selected from N, O and S, heterocyclyl or heterocyclylC 1-2 alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S;   wherein when R 8  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl, heteroarylC 1-2 alkyl, heterocyclyl, or heterocyclylC 1-2 alkyl, the C 3-6 cycloalkyl, phenyl, heteroaryl, or heterocyclyl motif is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 ;   R 9  represents cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; and wherein when R 8  is substituted C 3-6 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C═O) or sulfonyl (S(O) 2 ) group.   
     
     
         6 . A compound according to  claim 1 , wherein Z represents R 8 , wherein R 8  is C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, cyanoC 1-2 alkyl, C 1-3 haloalkyl, C 1-4 alkoxyC 2-4 alkyl, C 1-2 haloalkoxyC 2-4 alkyl, C 1-3 alkylcarbonylC 1-3 alkyl, C 1-3 alkoxycarbonylC 1-3 alkyl, or C 1-3 alkylcarbonyloxyC 2-4 alkyl; or
 R 8  is C 3-5 cycloalkyl, C 3-5 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl or heteroarylC 1-2 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, or 3 heteroatoms individually selected from N, O, and S, heterocyclyl or heterocyclylC 1-2 alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O, and S;   wherein when R 8  is C 3-5 cycloalkyl, C 3-5 cycloalkylC 1-2 alkyl, phenyl, phenylC 1-2 alkyl, heteroaryl, heteroarylC 1-2 alkyl, heterocyclyl, or heterocyclylC 1-2 alkyl, the C 3-5 cycloalkyl, phenyl, heteroaryl, or heterocyclyl motif is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 ;   R 9  represents cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl or methoxy; and wherein when R 8  is substituted C 3-5 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C═O) group.   
     
     
         7 . A compound according to  claim 1 , wherein Z represents R 8 , wherein R 8  is C 1-4 alkyl, C 3-4 alkenyl, C 1-3 haloalkyl, C 1-2 alkoxyC 2-3 alkyl or C 1-2 alkoxycarbonylC 1-2 alkyl; or
 R 8  is C 3-5 cycloalkyl, (C 3-5 cycloalkyl)methyl, phenyl, benzyl, heteroaryl, (heteroaryl)methyl, wherein the heteroaryl moiety is a 5-membered monocyclic aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O, and S, heterocyclyl or (heterocyclyl)methyl, wherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ring which comprises 1 or 2 heteroatoms individually selected from N and O;   wherein when R 8  is C 3-5 cycloalkyl, (C 3-5 cycloalkyl)methyl, phenyl, benzyl, heteroaryl, (heteroaryl)methyl, heterocyclyl, or (heterocyclyl)methyl, the C 3-5  cycloalkyl, phenyl, heteroaryl, or heterocyclyl motif is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 ;   R 9  represents cyano, fluoro, chloro, bromo, methyl or methoxy.   
     
     
         8 . A compound according to  claim 1 , wherein Z represents R 8 , wherein R 8  is methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, allyl, prop-1-enyl, isopropenyl, 1,1-difluoromethyl, 1,1,1-trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, methoxymethyl, methoxyethyl, methoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylmethyl, ethoxycarbonylethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, 2,2-difluorocyclopropylmethyl, 2,2-dichlorocyclopropylmethyl, phenyl, benzyl, 2-fluorophenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-fluoro-2-chlorophenyl, pyrazol-3-yl, pyrazol-4-yl, 1-methylpyrazol-3-yl, 1-methylpyrazol-4-yl, thiophene-2-yl, thiophene-3-yl, 2-methylthiophene-5-yl, 2-methylthiophene-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrofuran-2-yl methyl, tetrahydrofuran-3-yl methyl, morpholinyl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, or piperidin-4-yl. 
     
     
         9 . A compound according to  claim 1 , wherein Z represents —N(R 10 )R 11 , wherein R 10  represents hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, cyanoC 1-4 alkyl, hydroxyC 2-4 alkyl, C 1-2 alkoxyC 2-4 alkyl, C 1-2 haloalkoxyC 1-4 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, formyl, C 1-4 alkylcarbonyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, or C 1-4 alkylcarbonyloxyC 1-4 alkyl; or
 R 10  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, or phenylC 1-2 alkyl; 
 wherein when R 10  is C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-2 alkyl, phenyl, or phenylC 1-2 alkyl, the C 3-6 cycloalkyl or phenyl motif is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 12 ; 
 R 12  represents cyano, fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy; and wherein when R 10  is substituted C 3-6 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C═O) or sulfonyl (S(O) 2 ) group; and 
 R 11  represents hydrogen, hydroxy, C 1-4 alkyl, C 1-2 haloalkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 3-4 cycloalkyl, C 3-4 cycloalkylC 1-2 alkyl, C 1-4 alkoxy, C 3-4 alkenyloxy, or C 3-4 alkynyloxy. 
 
     
     
         10 . A compound according to  claim 1 , wherein Z represents —N(R 10 )R 11 , wherein R 10  is hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, cyanoC 1-2 alkyl, hydroxyC 2-4 alkyl, C 1-2 alkoxyC 2-4 alkyl, C 1-2 haloalkoxyC 1-2 alkyl, C 3-4 alkenyl, C 3-4 alkynyl, formyl, C 1-2 alkylcarbonyl, C 1-2 alkylcarbonylC 1-2 alkyl, C 1-2 alkoxycarbonylC 1-2 alkyl, or C 1-2 alkylcarbonyloxyC 1-2 alkyl; or
 R 10  is C 3-6 cycloalkyl or C 3-6 cycloalkylC 1-2 alkyl; 
 wherein when R 10  is C 3-6 cycloalkyl or C 3-6 cycloalkylC 1-2 alkyl, the C 3-6 cycloalkyl motif is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 12 . 
 R 12  represents cyano, fluoro, chloro, bromo, methyl, or methoxy; and wherein when R 10  is substituted C 3-6 cycloalkyl or heterocyclyl, these cycles may contain a carbonyl (C═O) group; and 
 R 11  represents hydrogen, hydroxyl, C 1-4 alkyl, C 1-2 haloalkyl, C 3-4 alkenyl, C 3-4 alkynyl, C 3-4 cycloalkyl, C 3-4 cycloalkylC 1-2 alkyl or C 1-4 alkoxy. 
 
     
     
         11 . A compound according to  claim 1 , wherein n is 0 or 1. 
     
     
         12 . An agrochemical composition comprising a fungicidally effective amount of a compound of Formula (I) according to  claim 1 . 
     
     
         13 . The composition according to  claim 12 , further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier. 
     
     
         14 . A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of Formula (I) according to  claim 1 , or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof. 
     
     
         15 . Use of a compound of Formula (I) according to  claim 1  as a fungicide.